Season 5: Episode 105: Drew's Reunion
The gang prepares for its high school reunion. Kate plans to spend all of her time with Patrick, a geeky classmate who is now a wealthy computer software magnate. Lewis poses as Bo Derek's driver at the airport and somehow manages to convince her to be his date at the reunion (as long as he doesn't touch her). Oswald hooks up with his old barber shop quartet. The speaker humiliates Drew by pointing out that he is single, still has the same job, and lives in his parents' house. Drew is confused when Kelly, the former head cheerleader, suddenly expresses an interest in him. Bo Derek explains that he is attractive to women because he is a nice, stable guy. Patrick shows up late, so Drew invites everyone back to the house for beer so that Kate can spend more time with him. An attractive woman gets revenge on Oswald for calling her names in high school (when she was fat) and ignoring her after they made out in his basement. Drew discovers that Kelly leads an extremely dysfunctional lifestyle and distances himself from her. Kate eavesdrops as Patrick seeks Drew's advice about her. Drew warns him not to wait twenty years to tell her how he feels, as no woman will ever be able to measure up to her. He admits that he has always loved her, but doesn't think he would have any chance with her. A shocked Kate breaks her date with Patrick. She goes into the house and asks Drew to dance.